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MILF's Boy: In Good Hands (MILF/boy)

Junior has been misbehaving at school. M decides he's not too old to spank but then gets a better idea when he seems humiliated to be half naked in front of her. She realizes that at his age there are better ways to get a boy to mind his M. She threatens him with chastity if he's bad but also shows him what his reward will be if he's good...she seduces him with her skilled, experienced hands...telling him that she can teach him everything about sexual pleasure & being a good lover...all he has to do is behave for Mmmmm...
Length: 10 minutes

Custom vid, no name mentioned. This is a sensual, teasing 'sex ed/masturbation encouragement' for you, my shy nephew who clearly has a fetish for pantyhose. I tell you it's okay for you to indulge your fetish with me, coaching you to masturbate along with me...it will be our little secret.
Length: 9 minutes

MILF asks her boy if he likes her sexy outfit. She wonders if he thinks her new boyfriend will like it. She teases him about his shyness...and his growing boner. She says she knows about him sniffing her dirty panties & pantyhose...and tells him to get a good sniff right from the source.
Length: 7 minutes

Taboo MILF hand job with orgasm control & sex ed! It's time you learn how to be a good lover. I'll teach you everything, how to lick pussy, how to please a women...today you'll start to learn orgasm control. I can see you are easily excited & prone to premature ejaculation. That just won't do! I'll bring you to the edge over & over, helping you practice holding off your orgasm...eventually allowing you to (enthusiastically) release. It's all just so naughty, isn't it?
Length: 11 minutes

As part of your sex ed I've gotten you a masturbation device to practice with (it's like a Fleshlight). I know it seems a little strange to have me (your MILF) teach you this stuff but I want to ensure you have proper instruction...& I also know that you secretly desire me even though it's so naughty & wrong...
Length: 16 minutes

Your MILF & I think it's time you learn more about sex. She's concerned you might turn out to be a bad lover if you don't get some coaching on orgasm control, safe sex, etc. So as an experienced woman & basically your Auntie who cares about you, I'm going to take you 'in hand' & help you out...
Length: 17 minutes

Do you have a thing for older women, mature ladies, MILF's, GILF's...experienced women who could show you the ropes, train you to be a better lover, to control your orgasm...a woman who can take control of you...
Length: 11 minutes

You're hot Aunt is visiting & finds out your marks have recently dropped in school. She figures out that you have a crush on your busty teacher making you so horny in class you can't focus. She takes matters in hand & shows you how to 'release the pressure'. She demonstrates various ways to masturbate, talks about lube, explains how to control your orgasm, etc. She tells you to look at her cleavage & that it's okay to fantasize about her breasts or your teachers breasts while masturbating. This will be our little secret.
Length: 12 minutes

I catch you wearing my panties. Uh-oh. I tease you about it & let you know that I've suspected you had a fetish for satin for awhile. I decide to indulge your perversions and guide you in a sensual masturbation instruction...
Length: 12 minutes

Custom vid...I come home from work and tell you to rub my feet. I notice this arouses you and start to tease you about your foot fetish. I tell you that your F***** could walk in any moment and what would he think of you! I let you worship my feet as I tell you about running into your ex & about how happy she is with her new boyfriend. I confide that she seems very sexually satisfied & that must really hurt your feelings since she dumped you for having a small penis. I encourage you to stroke your little dick while licking my feet, gently teasing & humiliating you...
Length: 10 minutes

You come home to find your MILF with your pal. She likes him...a lot...and decides to play with him right in front of you to humiliate you. She compares his BBC (Big Black Cock) to your little white dicket, & explains that THAT is why he gets to fuck you. Lots of teasing & humiliation...ending with you taking a HUGE LOAD of CUM all over your face!
Length: 13 minutes

Custom vid: I tell you, my boy Johnathon, to rub my feet. I then tell you that I ran into your ex, Katie & that she's just married a great guy & she's really happy. I can tell this makes you sad so I encourage you to stroke your "little peeps" while you worship my feet, to make you feel better. I go on to tell you that your ex had just returned from her honeymoon & I could tell by the sparkle in her eye that she had had lots of great sex. A woman can tell when another woman is being sexually satisfied. I explain that you could never make her feel that way because your penis is too small. I gently tease you about still being single, living at home with me while your ex is having a great life with a real man who probably has a much bigger cock, a better job, etc. I encourage you to cum while kissing my toes, reminding you that your place is kneeling before me, at my feet.
Length: 11 minutes

I have caught my boy looking at gay porn again. In an effort to put him on the STRAIGHT & narrow I combine 2 techniques: #1. I show him that he can be attracted to women by using my body & hands to arouse him. #2. I show him how awful it would be to be a fag by making him cum on his own face. If he were gay he'd have cocks & cum in his face & mouth all the time. I make sure that experience feels very humiliating & negative.
Length: 12 minutes

***A vid for my "special boys"***. You walk in on me going to the washroom. I tell you I'll be done in a moment so you might as well wait. While I'm washing my hands I tell you to go ahead if you have to 'go' so bad. I see that you're shy about going wee-wee in front of "ME". I offer to help but when I touch you your dinkie starts to get hard. I tease you about that & tell you you're going to have to leave the bathroom door open from now on & get used to me watching. I help you get rid of your boner so you can finally 'go'. MASTURBATION INSTRUCTION with very light HUMILIATION.
Length: 11 minutes

I always wanted a little girl, not a boy...so I dress my boy up like a girl. Before sending him/her off to school I milk him to ensure he doesn't pop a woody at school, which would raise some questions. While stroking him I tell him how I'll have to train him to be the perfect cock sucker in case a man tries to diddle him. That way he can keep them from going into 'her' panties by making him cum in 'her' mouth.
Length: 10 minutes

To ensure her boy doesn't grow up to be a homosexual, a strict, church-going "MILF" takes matters into her own hands. A little bit of disciplinary spanking puts her boy in his place before she shows him how good it can feel to cum by a woman's hand.
Length: 13 minutes

This is a gentle, sweet instructional situation with an intelligent, sexy "MILF" who wants to ensure her boy grows up to be a good lover. She catches him playing with her dirty panties which prompts her to take matters into her own hands. There's a long, slow teasing build up, lots of light touching through his shorts...a little sensual foot worship (where she explains he should worship a woman's foot like he would lick her pussy)...she demonstrates good oral skills, explaining the similarities of a penis & a pussy...she then shows him how to use a condom correctly & helps him get used to the sensation of intercourse while wearing a condom. All the while he is instructed to control his orgasm, he's edged & encouraged to take his time & enjoy the experience. There's no rush. There's a nice long hand job at the end where he's edged & teased...eventually erupting in a long built-up orgasm. He's lovingly chastised for not asking for permission as he was instructed. She continues to stroke his sensitive cock a little as punishment while he squirms & giggles. She teases that she'll smear his cum on her pussy & make him lick it off. It's light, loving, kinky discipline. He's left feeling that he has to work a little harder to please "MILF", & he has a lot of practicing to do, but he's in good hands with a experienced mature woman who takes a keen interest in his education. (This is a custom vid. I use the name 'Tommy' a few times.)
Length: 22 minutes

Before my boy goes off to college I decide to teach him about the birds & the bees. Who better to teach him than the loving mature woman who raised him to respect women? Today's lesson is primarily about learning to please a woman with his mouth. 1st I give detailed instructions, then I have him practice until I have a 100% real orgasm (not a fake porn orgasm). I then reward him by showing him what fellatio is & finish him with a hand job. The message throughout is to respect & worship women. To use his cock, hands & mouth to please a woman FIRST. Lots of SEX EDUCATION & real-world training on being a good lover & a gentleman.
Length: 23 minutes